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Paper | Regular issue | Vol 57, No. 11, 2002, pp.2065-2079
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9575
Photocycloaddition of 1,3-Diphenyl-N-methyl Enaminoketonatoboron Difluoride with Simple Olefins

Kuniaki Itoh,* Kazuhiko Okazaki, and Yoshito Toyotomi

*Department of Chemistry, Faculty of Science, Kobe University, Nada-Ku, Kobe 6557-8501, Japan

Abstract

The photoaddition of some cyclic and acyclic olefins to (N-B)-Z-1-difluoroboryloxy-1,3-diphenyl-3-methylimino-1-propene (BF2-complex (1)) is discussed. Some of the resulting [2+2] photoadducts produce cyclobutane derivatives having cis configurations. The rearrangements of the cyclobutanes give pyridinium salts and 1,5-diketones. Reaction schemes for the formation of the cyclobutanes are presented. The dimer of the BF2-complex (1) is also formed in a reaction which is in competition with the olefins photoaddition.